Faculty Publications
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Item New quinoline derivatives: Synthesis and investigation of antibacterial and antituberculosis properties(Elsevier Masson SAS, 2010) Eswaran, S.; Vasudeva Adhikari, A.V.; Chowdhury, I.H.; Pal, N.K.; Thomas, K.D.Four new series of quinoline derivatives were synthesized starting from 2-trifluoromethyl aniline through multi-step reactions. In the reaction sequence,substituted aniline was cyclized to 4-hydroxy quinoline 1,which was then transformed to 4-chloro-2,8-bis(trifluoromethyl)quinoline 2. The key scaffold 4-hydrazinyl-2,8-bis(trifluoromethyl)quinoline 3,obtained from the compound 2,was successfully converted to target quinoline derivatives,viz. hydrazones 4aet,ureas 5aee,thioureas 6aec and pyrazoles 7aed,in good yields. The newly synthesized title compounds were evaluated for their in vitro antibacterial activity against Escherichia coli,Staphylococcus aureus,Pseudomonas aeruginosa and Klebsiella pneumoniae (recultured) and antituberculosis activity against Mycobacterium tuberculosis H37Rv and MDR-TB. Preliminary results indicated that most of the hydrazone derivatives demonstrated very good antibacterial and antituberculosis activities while other derivatives showed moderate activity. © 2010 Elsevier Masson SAS. All rights reserved.Item Design and synthesis of some new quinoline-3-carbohydrazone derivatives as potential antimycobacterial agents(Elsevier Ltd, 2010) Eswaran, S.; Vasudeva Adhikari, A.V.; Pal, N.K.; Chowdhury, I.H.A series of 26 new quinoline derivatives carrying active pharmacophores has been synthesized and evaluated for their in vitro antituberculosis activity against Mycobacterium tuberculosis H37Rv (MTB), Mycobacterium smegmatis (MC2), and Mycobacterium fortuitum following the broth micro dilution assay method. Compounds 13e, 13i, 13k, 14a, 14c, 14i, and 14k exhibited significant minimum inhibition concentrations, when compared with first line drugs isoniazid (INH) and rifampicin (RIF) and could be ideally suited for further modifications to obtain more efficacious compounds in the fight against multi-drug resistant tuberculosis. © 2009 Elsevier Ltd. All rights reserved.Item New 1,3-oxazolo[4,5-c]quinoline derivatives: Synthesis and evaluation of antibacterial and antituberculosis properties(2010) Eswaran, S.; Vasudeva Adhikari, A.V.; Ajay Kumar, R.A new class of fused oxazoloquinoline derivatives was synthesized starting from 2-bromo-1-phenylethanones 1a-b through multi-step reactions. The newly synthesized compounds were evaluated for their in vitro antibacterial against Escherichia coli (ATTC-25922), Staphylococcus aureus (ATTC-25923), Pseudomonas aeruginosa (ATCC-27853) and Klebsiella pneumoniae (recultured) and antituberculosis activity against Mycobacterium tuberculosis H37Rv (ATCC 27294). Preliminary results indicated that most of the compounds demonstrated very good antibacterial and antituberculosis activities which are comparable with the first line drugs. Compounds 6a, 6c, 6g, 6j, 6k and 6n emerged as the lead antitubercular agents with MIC, 1 ?g/mL and 99% bacterial inhibition while eight compounds, viz., 5a, 15k, 6a, 6c, 6g, 6j, 6k and 6n were found to be more potent than INH (MIC: 1.5 ?g/mL) with MIC 1 ?g/mL. © 2009 Elsevier Masson SAS. All rights reserved.Item New quinolin-4-yl-1,2,3-triazoles carrying amides, sulphonamides and amidopiperazines as potential antitubercular agents(2011) Thomas, K.D.; Vasudeva Adhikari, A.V.; Chowdhury, I.H.; Sumesh, E.; Pal, N.K.Three new series of quinoline-4-yl-1,2,3-triazoles carrying amides, sulphonamides and amidopiperazines were synthesized through multi-step reactions. The required intermediate, [1-(6-methoxy-2-methylquinolin-4-yl)-1H-1, 2,3-triazol-4-yl]methanol (2) was prepared by treating 4-azido-6-methoxy-2- methylquinoline (1) with propargyl alcohol. Three different series of compounds were synthesized from this intermediate. All the newly synthesized compounds were characterized by spectral and elemental analyses. The structure of 2 was confirmed by X-ray crystallographic study. Further, the title compounds were evaluated for their in vitro anti-bacterial activity against five different bacterial strains and antimycobacterial activity against Mycobacterium tuberculosis H37Rv, Mycobacterium smegmatis (ATCC 19420) and Mycobacterium fortuitum (ATCC 19542). Title compounds, 6a, 6d, 6i, 6j, 7e, 10a and 10i were found to be active against Mycobacterium tuberculosis H37Rv strain and could be lead molecules of interest. © 2011 Elsevier Masson SAS.Item Design, synthesis and docking studies of quinoline-oxazolidinone hybrid molecules and their antitubercular properties(2011) Thomas, K.D.; Vasudeva Adhikari, A.V.; Chowdhury, I.H.; Sandeep, T.; Mahmood, R.; Bhattacharya, B.; Sumesh, E.New series of quinoline-oxazolidinone hybrid molecules were synthesized based on the preliminary docking studies. All the newly synthesized compounds were characterized by spectral analyses. The newly synthesized compounds were screened for their antimycobacterial properties based on the promising preliminary antibacterial screening results. Amongst tested compounds, compounds 8a, 8j and 13a were active at 0.65 ?g/mL against Mycobacterium tuberculosis H 37Rv strain. The mode of action of these active compounds was carried out by docking of receptor enoyl-ACP reductase with newly synthesized candidate ligands 8a, 8j and 13a. These compounds exhibited well established bonds with one or more amino acids in the receptor active pocket. From the docking studies, compound 8j was considered to be the best inhibitor. © 2011 Elsevier Masson SAS. All rights reserved.